P
US9502669B2ActiveUtilityPatentIndex 81

Organic light emitting diode

Assignee: LG CHEMICAL LTDPriority: Aug 12, 2014Filed: Jul 16, 2015Granted: Nov 22, 2016
Est. expiryAug 12, 2034(~8.1 yrs left)· nominal 20-yr term from priority
Inventors:HUH JUNGOHLEE DONG HOONCHUN MINSEUNGJANG BOONJAEJUNG Wonik
H01L 2251/558C09K 2211/1011H01L 51/0054C09K 2211/1014C09K 11/06C09K 11/025H01L 51/5092H01L 51/0067H01L 51/0072H01L 51/5072H01L 51/0052H10K 50/16H10K 85/649H10K 50/171H10K 85/615H10K 85/622H10K 85/626H10K 85/654H10K 50/165H10K 50/166H10K 85/6572H10K 85/633
81
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16
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Claims

Abstract

The present specification relates to an organic light emitting diode.

Claims

exact text as granted — not AI-modified
The invention claimed is: 
     
       1. An organic light emitting diode comprising:
 a cathode; 
 an anode provided to face the cathode; 
 a light emitting layer provided between the cathode and the anode; 
 an electron transporting layer provided between the cathode and the light emitting layer; and 
 an electron adjusting layer provided between the light emitting layer and the electron transporting layer, 
 wherein the electron transporting layer comprises an organic compound containing an aromatic hetero ring, 
 the electron adjusting layer comprises a heterocyclic compound represented by the following Formula 1, and 
 an ionization potential (Ip m ) of the electron transporting layer is larger than an ionization potential (IP a ) of the electron adjusting layer: 
 
       
         
           
           
               
               
           
         
         in Formula 1, 
         X1 is CR1 or N and X2 is CR2 or N, 
         Y1 is CR5 or N, Y2 is CR6 or N, Y3 is CR7 or N, and Y4 is CR8 or N, 
         Z1 is CR9 or N, Z2 is CR10 or N, Z3 is CR11 or N, and Z4 is CR12 or N, 
         X1, X2, Y1 to Y4, and Z1 to Z4 are not simultaneously N, and 
         R1, R2, and R5 to R12 are the same as or different from each other, and are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; or a substituted or unsubstituted phosphine oxide group, or adjacent substituents of R1, R2, and R5 to R12 combine with each other to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted hetero ring. 
       
     
     
       2. The organic light emitting diode of  claim 1 , wherein the electron adjusting layer is provided to be in contact with the light emitting layer. 
     
     
       3. The organic light emitting diode of  claim 1 , wherein a thickness of the electron transporting layer is larger than a thickness of the electron adjusting layer. 
     
     
       4. The organic light emitting diode of  claim 1 , wherein the heterocyclic compound represented by Formula 1 is represented by the following Formula 1A or 1B: 
       
         
           
           
               
               
           
         
         in Formulae 1A and 1B, 
         Y1 to Y4, Z1 to Z4, and R2 are the same as those defined in Formula 1, 
         X3 to X6 are the same as or different from each other, and are each independently CR3 or N, and 
         R3's are each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; or a substituted or unsubstituted phosphine oxide group, or adjacent substituents combine with each other to form a substituted or unsubstituted hydrocarbon ring; or a substituted or unsubstituted hetero ring. 
       
     
     
       5. The organic light emitting diode of  claim 1 , wherein the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulae 1-1 to 1-4: 
       
         
           
           
               
               
           
         
         in Formulae 1-1 to 1-4, 
         a, b, and c are each an integer of 1 to 4, 
         d and e are each an integer of 1 to 6, and 
         when a, b, c, d, and e are each an integer of 2 or more, the two or more structures in the parenthesis are the same as or different from each other, and 
         A1 to A5 and R2 are the same as or different from each other, and each independently hydrogen; deuterium; a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms; or a substituted or unsubstituted phosphine oxide group. 
       
     
     
       6. The organic light emitting diode of  claim 1 , wherein at least one of R1, R2, and R5 to R12 is an aryl group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group; or a phosphine oxide group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group, or adjacent substituents combine with each other to form a hydrocarbon ring which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of a cyano group, an aryl group, a heterocyclic group, and a phosphine oxide group. 
     
     
       7. The organic light emitting diode of  claim 1 , wherein the heterocyclic compound represented by Formula 1 is represented by any one of the following Formulae 1-1-1 to 1-1-7, 1-2-1 to 1-2-10, 1-3-1 to 1-3-5, and 1-4-1 to 1-4-7: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       8. The organic light emitting diode of  claim 1 , wherein the electron transporting layer comprises an organic compound containing an aromatic hetero ring represented by the following Formula 2: 
       
         
           
           
               
               
           
         
         in Formula 2, 
         X5 and X6 are the same as or different from each other, and are each independently N or CH, and 
         Ar1 to Ar3 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms. 
       
     
     
       9. The organic light emitting diode of  claim 8 , wherein Ar1 and Ar3 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; a substituted or unsubstituted biphenyl group; a substituted or unsubstituted naphthyl group; or a substituted or unsubstituted fluorenyl group. 
     
     
       10. The organic light emitting diode of  claim 8 , wherein at least one of Ar1 to Ar3 is represented by the following Formula 3: 
       
         
           
           
               
               
           
         
         in Formula 3, 
         o, p, and q are 0 or 1, 
         1≦o+p+q≦3, 
         r is 1 or 2, and 
         when r is 2, two Ar's are the same as or different from each other, 
         L1 to L3 are the same as or different from each other, and are each independently a phenylene group; or a naphthalene group; or a fluorenylene group, and 
         Ar is an aryl group which is unsubstituted or substituted with one or two or substituents selected from the group consisting of an aryl group and a heterocyclic group; or a heterocyclic group which is unsubstituted or substituted with one or two or more substituents selected from the group consisting of an aryl group and a heterocyclic group. 
       
     
     
       11. The organic light emitting diode of  claim 8 , wherein the organic compound containing the aromatic hetero ring represented by Formula 2 is represented by any one of the following Formulae 2-1 to 2-13: 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       12. The organic light emitting diode of  claim 1 , wherein the organic light emitting diode emits blue fluorescent light. 
     
     
       13. The organic light emitting diode of  claim 1 , wherein the organic light emitting diode further comprises one or two or more layers selected from the group consisting of a hole injection layer, a hole transporting layer, an electron transporting layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.

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